(E)-3-(2-phenylethenyl)-1,1'-biphenyl | 52500-13-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-3-(2-phenylethenyl)-1,1'-biphenyl
• 英文别名: 1-Phenyl-2-trans-(biphenylyl)-aethylen；(E)-3-styrylbiphenyl；1-phenyl-3-[(E)-2-phenylethenyl]benzene
• CAS: 52500-13-7
• 化学式: C₂₀H₁₆
• 分子量: 256.347
• InChiKey: HXAUAWSDMXHAND-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-phenylethenyl)-1,1'-biphenyl 在 potassium tert-butylate 、 溴 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 8.0h， 生成 1-(m-biphenylyl)-2-phenylethyne
  参考文献：
  名称：

  The First Aryne Evolution from the Reactions of Selenonium Salts with Aryllithiums

  摘要：

  The first example of the benzyne generation was found in the reactions of alkynylselenonium salt 1a with 1.0 equiv. of phenyllithium in THF at room temperature for 3 h. The formation of the aryne intermediate was confirmed in the reactions of alkynylselenonium salt 1b and tri-p-tolylselenonium salt 6b with tolyllithium, which gave a mixture of alkynylbiphenyl derivatives 18 and 19 in 19% yield (18:19=11:8) and a mixture of bitolyls 28 and 29 in 63% yield (28:29=2:1), respectively. The reaction mechanisms of these reactions are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01090-x
• 作为产物：
  描述：

  间氯溴苯 在 四丁基醋酸铵 、 palladium diacetate 、 caesium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (E)-3-(2-phenylethenyl)-1,1'-biphenyl
  参考文献：
  名称：

  Pd nanoparticle catalysed one-pot sequential Heck and Suzuki couplings of bromo-chloroarenes in ionic liquids and water

  摘要：

  在绿色反应介质（例如离子液体和水）中生成的Pd纳米粒子催化了溴氯芳烃的单锅顺序Heck和铃木偶联反应，获得了不对称取代的芳烃，产率良好。

  DOI：

  10.1039/c1ob06385e

文献信息

• Build-up of double carbohelicenes using nitroarenes: dual role of the nitro functionality as an activating and leaving group
  作者：Fulin Zhou、Fujian Zhou、Rongchuan Su、Yudong Yang、Jingsong You

  DOI：10.1039/d0sc02058c

  日期：——

  streamlined and simplified synthetic route to double carbohelicenes starting from nitroarenes through sequential nitro-activated ortho-C–H arylation, denitrative alkenylation and intramolecular cyclodehydrogenation. In this synthetic strategy, the nitro group plays a dual role namely as a leaving group for the denitrative alkenylation and as an activating group for ortho-C–H arylation, which is distinct

  双碳烯的构建是一项非常有趣但具有挑战性的工作。本文公开了从硝基芳烃开始，通过顺序硝基活化的邻-C-H芳基化、脱硝基烯基化和分子内环脱氢来生产双碳螺旋烯的精简且简化的合成路线。在该合成策略中，硝基发挥双重作用，即作为脱硝烯基化的离去基团和作为邻-C-H芳基化的活化基团，这与传统偶联反应中的芳基卤化物不同。在这项工作中，提出了钯催化的硝基芳烃的 Heck 型烯基化反应，其中传统惰性的 Ar-NO 2键被裂解。这项工作为多环芳烃（PAH）提供了一种新颖的合成策略。
• Room-Temperature <i>meta</i>-Functionalization: Pd(II)-Catalyzed Synthesis of 1,3,5-Trialkenyl Arene and <i>meta</i>-Hydroxylated Olefin
  作者：Milan Bera、Santosh K. Sahoo、Debabrata Maiti

  DOI：10.1021/acscatal.6b00675

  日期：2016.6.3

  reactions at room temperature continues to be a tough challenge. Use of a phosphonate linkage allowed a Pd (II)-catalyzed meta-C–H functionalization at room temperature while incorporating a cyanophenol-based directing moiety. Successful implementation of sequential di-meta-olefination led to the synthesis of a trialkenyl arene, which has applications in organic electronics and optoelectronics. Under robust

  在室温下发展间位-C-H官能化反应仍然是一个艰巨的挑战。膦酸酯键的使用允许Pd（II）在室温下催化间位C–H官能化，同时引入基于氰基酚的导向部分。顺序二元间烯烃的成功实施导致了三烯基芳烃的合成，该三烯基芳烃已在有机电子学和光电子学中得到应用。在稳定的条件下，已经发现了C-O键形成的间位羟基化和间位乙酰氧基化。
• Synthesis of Stilbene and Distyrylbenzene Derivatives through Rhodium-Catalyzed<i>Ortho</i>-Olefination and Decarboxylation of Benzoic Acids
  作者：Satoshi Mochida、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol1027392

  日期：2010.12.17

  Ortho-substituted benzoic acids efficiently undergo precisely ordered ortho-olefination/decarboxylation upon treatment with styrenes in the presence of a rhodium catalyst and silver salt oxidant to afford the corresponding meta-substituted stilbene derivatives. The selective syntheses of 1,3- and 1,4-distyrylbenzenes have also been realized through the reactions of simple benzoic acid and phthalic

  邻-取代的苯甲酸有效离岗精确有序邻-olefination /脱羧在与在铑催化剂和银盐氧化剂，得到相应的存在的苯乙烯治疗间-取代的二苯乙烯衍生物。1，3-和1，4-二苯乙烯基苯的选择性合成也已经通过在相似条件下分别通过简单的苯甲酸和邻苯二甲酸与苯乙烯的反应来实现。
• Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group
  作者：Satoshi Mochida、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo200509m

  日期：2011.5.6

  The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. alpha,beta-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the beta-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.
• Palladium-Catalyzed Denitrative Mizoroki–Heck Reactions of Aryl or Alkyl Olefins with Nitrobenzenes
  作者：Y. Peng、Z. Li、J. Hu、T. Wu

  DOI：10.1134/s1070428022120168

  日期：2022.12